Holiday rentals in The Loop

Modern design with VU Skyward rooftop bar

Refundable Incidental hold of $75/day required at check in. Must be 21+ to book/stay. We are connected to McCormick Place Convention Center and Wintrust Arena via sky-bridge. The nearby subway train brings guests to Millennium Park and downtown attractions. Soldier Field and the Museum Campus are within a mile are within a mile. Guests can enjoy a view of Chicago and Lake Michigan at our VU Skyward rooftop bar. We also have a Starbucks in our lobby. Self Parking is available for $52/night.

Treetop Oasis With Parking Walk To Town & Train

Take a deep breath and relax in this airy and bright top floor apartment. Treetops surround the newly renovated and spacious home in a premier Oak Park location. 20 min. to downtown Chicago. Only 1/2 block to the FLW Home & Studio. Walk to dining & train. 2 bedrooms & 1 bath w/tub & shower. Open living/dining/kitchen/sunroom. Wow kitchen w/huge island. Primary w/king bed + deep closet. 2nd bdrm w/built-in bunk beds + desk + balcony. Private entry & deck. Shared fenced yard. Driveway parking.

Deluxe King Room · Juliette Balcony · Sono B&B

You’ll be charmed by this private guest room inside The Sono Chicago Bed and Breakfast, a newly built boutique B&B in the heart of Chicago’s historic Old Town. This listing is for one private king room with a Juliette balcony within a shared bed and breakfast. Guests enjoy their own bedroom and ensuite space. Complimentary breakfast is included each morning. We’re located on a quiet, tree-lined street and offer cozy accommodations, warm hospitality, and a welcoming sense of community.

Central Loop Hotel

After a day of exploring the city, unwind in your spacious standard room featuring premium bedding and thoughtfully placed charging points. Stay productive with a multipurpose workspace, ergonomic chair, and task lighting, or relax with lightning-fast free Wi-Fi and a flat-screen smart TV. Enjoy a Nespresso brewer with complimentary coffee and tea, plus in-room yoga mat and resistance bands for your wellness. Bathroom amenities include C.O. Bigelow products, toiletries & hair dryer.

Zen in La Grange Park

Relax. Recharge. Explore. Welcome to Zen, your peaceful retreat in beautiful La Grange Park. This charming 2-bedroom ranch offers the perfect blend of comfort and convenience with spacious living areas, a fully fenced backyard, and an attached 2-car garage — ideal for families, friends, or extended stays. Nestled in a quiet neighborhood, you’ll enjoy a relaxing atmosphere while being just minutes from nearby trains and bus stations that provide easy access to Downtown Chicago.

DT Oak Park Luxe|3BR 2BA+Yard|15 min to Chicago

Welcome! Location location location! Relax in this newly renovated 3-bedroom home in the heart of the historic district. Steps from the Frank Lloyd Wright Home and Studio, Hemingway Birthplace Museum, shops, dining, and easy transit to downtown Chicago. Stylish, spotless, and family-friendly — the perfect blend of comfort and charm. No parties, events, gatherings, weapons, dangerous items or disruptive behavior allowed. Every adult must be on the reservation. No exceptions.

Arlo Chicago

Step into the city king room where inspiring views of downtown and a spacious cozy king bed invite you to relax in style. Enjoy smart amenities like a Nespresso coffee machine, a 55 inch flat screen TV, a smart fridge and a work desk. Contemporary luxury design and thoughtful details like a hand held steamer hair dryer and laptop sized safe make this a perfect home base whether you are exploring the city or enjoying a quiet night in.

Riu Plaza Chicago

The deluxe family king room is a perfect choice for families visiting Chicago, offering plenty of space and comfort for your city getaway. Enjoy amenities like central heating, air conditioning, and an in-room safe to ensure a relaxing stay. A small fridge, coffee maker, and sofa bed add extra convenience for your family. Practical touches such as a shower, hairdryer, and iron are also included for your comfort.

Spacious Oak Park 4bd/3.5ba and Parking

Unwind in our classic 4 bedroom, single-family home in Oak Park. It’s perfect for families or groups, offering you a fully equipped gourmet kitchen, 2 living spaces, 3.5 bathrooms, 4 dedicated work spaces, a backyard oasis and parking. With its historic charm, proximity to Frank Lloyd Wright's architecture, Columbus Park and easy access to the expressway, it's central for exploring Oak Park's cultural gems.

Close to Navy Pier + Restaurant. Bar. Gym.

Tucked just off the Magnificent Mile, Hotel Saint Clair gives you front-row access to Chicago’s must-sees—think Navy Pier, Millennium Park, and late-night eats around the corner. Sip your morning coffee, grab your camera, and hit the lakefront in minutes. The rooms are pet-friendly, WiFi’s on the house, and everything you want to see is walkable. It’s your laid-back launchpad for big city adventures.

Millennium Knickerbocker Hotel Chicago, Standard...

Standard room offers a tastefully decorated space with a plush king bed designed for your comfort and relaxation. Enjoy modern amenities like WiFi, smart TV and an in room safe along with coffee and tea making facilities. Thoughtful touches create a welcoming atmosphere for both work and leisure making it an ideal choice for any traveller. Unwind and recharge in style during your stay.

A polished, modern affair on iconic Michigan Ave.

Experience an upgraded stay at Le Méridien Essex Chicago, located on Michigan Ave in the city's heart. Our luxury hotel, surrounded by iconic attractions, offers modern rooms with stunning views of Grant Park, Lake Michigan, Buckingham Fountain, and the Museum Campus. We're committed to making your stay in the Loop unforgettable.